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Corporate Runaways

Overland travelers and certified geeks, based in Vermont.


3-Minute Read

Living in Boston there’s not a lot a lot of places to practice riding on dirt, but there is the Trans-Massachusetts Trail, which hooks up with the Puppy Dog Route (maps here) at its north end and continues north to the Canadian border. We’ll be doing the Puppy Dog soon, but in the meantime the TMT makes for a good day trip, and  being a collection of roads specifically chosen for people unfamiliar with dirt riding it was a great choice for introducing Dachary to dirt.

For the impatient, here’s the improved GPX file for your Garmin GPSs:  TMT v2.0

It’s the same route as the original TMT, but it’ll have the GPS follow the road whenever possible instead of pointing straight to the next waypoint.

Barely a mile into it a poorly placed dead-end sign and a GPS map that could have been better lead us to going the wrong way, nearly colliding because I was focusing on the GPS and my brain was still in on-road mode and using front brakes and ABS instead of rear-brakes with the ABS off. Then, reversing down the hill Dachary dropped her bike for the first time at zero mph. Of course, we had to document the moment.

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As an aside, I am so happy she’s gotten a Rev’It Sand Jacket since then. Besides the fact that the Rev’It is about 40 times better quality, that Joe Rocket is about as flattering as an inner-tube.

The roads were pretty much as advertised, pretty, tree-lined, hard packed, and easy going.

A typical road on the TMT

The only exception was when we took another wrong turn (poor GPS map) and encountered the cows.


We checked the map and it turned out that we could just do three sides of a box and meet back up with the road we’d accidentally left. The last side had a “road closed to through traffic” sign on it, which we didn’t think much about (see the map below the post). You see those all the time when they’re doing construction. It usually just means they want to keep the traffic to a minimum. Not this time though. The road was literally closed to through traffic. Water had cut squirrelly little ditches that went back and forth across the hill, there was an exposed pipe that we both managed to whack our bash plates on, and at the bottom they’d placed a couple Jersey Barriers across the road to prevent anyone from going through. If someone hadn’t already pulled them apart just enough for a small ATVs or motorcycles we’d have had to turn around. I’ve no idea what a car would be expected to do at that point.

The road was physically closed.

It was simultaneously the worst and best road of the trip. Just a short little diversion that changed everything. Having dropped her bike so soon on the dirt Dachary was a bit apprehensive about the whole lack of traction thing, but after making it through this her confidence soared and everything else was cake, which is great because most of the beautiful things we want to see in South America are far from pavement.

Corn Harvesting

Closed, but not really

Deerfield River Bridge

People Fishing in the Deerfield River

Road Closed For Winter

Well… everything was cake until the bear.

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A couple with 2 dogs and a thirst for exploring the places in-between.